6 days in Massachusetts Itinerary

6 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner

This plan was created by another user. Make it your plan

Route & dates

6 days in Massachusetts Itinerary

Start: Orlando, Florida
+2
Fly + Taxi + Ferry:  7 h 15 min
1
Oak Bluffs, Martha's Vineyard
— 1 night
Drive:  2 h 15 min
2
Chatham
— 2 nights
Drive:  2 h
3
Boston
— 2 nights
Fly:  5 h
End: Orlando, Florida

1
night
Oak Bluffs, Martha's Vineyard

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 16th (Sat): take in the dramatic natural features at Aquinnah Cliffs, enjoy the sea views from Edgartown Lighthouse, then make a trip to Flying Horses Carousel, and finally take a stroll through Martha's Vineyard Camp meeting Association (MVCMA).

For photos, other places to visit, more things to do, and tourist information, go to the Oak Bluffs trip maker app .

Orlando to Oak Bluffs is an approximately 7.5-hour combination of flight and ferry. You can also fly; or do a combination of flight, bus, and ferry. Traveling from Orlando in November, expect Oak Bluffs to be much colder, temps between 53°F and 37°F. Cap off your sightseeing on the 16th (Sat) early enough to go by car to Chatham.

Things to do in Oak Bluffs

Historic Sites Neighborhoods Nature

Side Trips

Edgartown Lighthouse, Aquinnah Cliffs
Find places to stay Nov 15 — 16:
Highlights from your plan
Edgartown Lighthouse ©
Edgartown Lighthouse
Flying Horses Carousel ©
Flying Horses Carousel

2
nights
Chatham

Chatham ©
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Start off your visit on the 17th (Sun): enjoy the sand and surf at Coast Guard Beach, enjoy the sand and surf at Herring Cove Beach, and then browse the collection at Provincetown Library. On the next day, take an in-depth tour of Salt Pond Visitor Center, then tour the pleasant surroundings at Nauset Beach, and then take in the waterfront at Chatham Pier and Fish Market.

To find other places to visit, where to stay, traveler tips, and tourist information, refer to the Chatham trip planner.

Traveling by car from Oak Bluffs to Chatham takes 2.5 hours. In November, daily temperatures in Chatham can reach 52°F, while at night they dip to 39°F. Finish your sightseeing early on the 18th (Mon) to allow enough time to drive to Boston.

Things to do in Chatham

Outdoors Parks Beaches

Side Trips

Eastham, Provincetown, Nauset Beach
Find places to stay Nov 16 — 18:
Highlights from your plan
Herring Cove Beach ©
Herring Cove Beach
Chatham Pier and Fish Market ©
Chatham Pier and Fish Market
Salt Pond Visitor Center ©
Salt Pond Visitor Center

2
nights
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Start off your visit on the 19th (Tue): take an in-depth tour of Old State House, then admire the masterpieces at Museum of Fine Arts, and then admire the natural beauty at Boston Public Garden. On the 20th (Wed), you'll have a packed day of sightseeing: appreciate the extensive heritage of Freedom Trail, buy something for everyone on your list at Faneuil Hall Marketplace, and then stroll around Boston Common.

To see traveler tips, maps, where to stay, and other tourist information, go to the Boston trip itinerary maker .

Traveling by car from Chatham to Boston takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 52°F in November, and nighttime lows around 37°F. Wrap up your sightseeing on the 20th (Wed) to allow time to travel back home.

Things to do in Boston

Museums Parks Historic Sites
Find places to stay Nov 18 — 20:
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Freedom Trail ©
Freedom Trail

Similar Plans

10 days in Massachusetts BY A USER FROM UNITED STATES October, culture, outdoors, historic sites, museums, popular sights PREFERENCES: October, culture, outdoors, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Massachusetts BY A USER FROM UNITED STATES September, culture, outdoors, romantic, historic sites, fast-paced, popular & hidden gems PREFERENCES: September, culture, outdoors, romantic, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 8 days in Massachusetts BY A USER FROM UNITED STATES September, culture, historic sites, museums, fast-paced, popular sights PREFERENCES: September, culture, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Fast-paced 7 days in Massachusetts BY A USER FROM UNITED STATES October, culture, outdoors, historic sites, museums, slow & easy, popular & hidden gems PREFERENCES: October, culture, outdoors, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 9 days in United States BY A USER FROM UNITED STATES April, culture, outdoors, romantic, historic sites, hidden gems PREFERENCES: April, culture, outdoors, romantic, historic sites ATTRACTION STYLE: Hidden gems PACE: Medium 8 days in United States BY A USER FROM UNITED STATES April, culture, outdoors, romantic, wildlife, popular sights PREFERENCES: April, culture, outdoors, romantic, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 8 days in United States BY A USER FROM UNITED STATES April, culture, outdoors, romantic, shopping, popular sights PREFERENCES: April, culture, outdoors, romantic, shopping ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Massachusetts BY A USER FROM UNITED STATES March, teens, popular sights PREFERENCES: March, teens ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Massachusetts & Vermont BY A USER FROM ISRAEL October, kids, outdoors, relaxing, museums, shopping, wildlife, slow & easy, popular sights PREFERENCES: October, kids, outdoors, relaxing, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 7 days in Massachusetts BY A USER FROM UNITED STATES October, popular sights PREFERENCES: October ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Massachusetts BY A USER FROM UNITED STATES September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Massachusetts BY A USER FROM UNITED STATES October, popular sights PREFERENCES: October ATTRACTION STYLE: Popular sights PACE: Medium
See more plans